Exercise No.

13
Reactions and Preparations of Ethers and Epoxides

1. Predict the major products (if any) of the reaction of isobutyl-n-propyl ether with:
a. conc. NaOH NO REACTION
b. H2Cr2O7, room temp. NO REACTION
c. dilute aq. H2SO4 Isobutanol & Propanol
d. hot conc. HBr Isobutanol & 1-iodopropane

2. Find the products of the following reactions.

CH3CH=CH2 + H20
a. CH3(CH2)2OH + H2SO4 180 C
o Propene + Water

140 oC CH3CH2CH2 -O-CH3CH2CH2 + H20

Dipropyl ether + Water

b. CH3ONa + CH3(CH2)3Br CH3 -O-CH2CH2CH2CH3

Butyl methyl ether

O Br OH
c.
+ HBr

2-bromocyclohexanol

CH3-CH-CH-CH3 + C6H5COOH
d. CH3CH=CCH3 + C6H5COOOH
O
2,3-epoxy-butane + benzoic acid

e.
OH
O + CH3MgBr

CH3

2-methylcyclohexanol

3. Write the major products of the reaction of ethylene oxide with each of the following:
a. HI
CH2 - CH2 + HI CH2 - CH2

O I OH
Ethylene iodohydrin / 2-iodoethanol

b. aq. KOH
CH2 - CH2

CH2 - CH2 KOH

OH OH
H20
Ethylene glycol
O

CH2 - CH2
c. H2SO4 in CH3CH2CH2OH as solvent
CH3CH2CH2OH CH3CH2CH2O OH
CH2 - CH2
2-propoxyethanol
O H2SO4
 d. CH3CH2CH2CH2MgBr
CH3CH2CH2CH2CH2CH2OH
CH2 - CH2 + CH3CH2CH2CH2MgBr hexanol
O

e. CH3CH2NH2

CH2 - CH2 + CH3CH2NH2 CH3- CH2 -NH - CH2 - CH2 - OH

2-ethylaminoethanol
O

4. Starting with an appropriate alcohol, outline the method of synthesis of each of the
following:
a. CH3-O-CHCH3
CH3

CH3 CH Br

CH3OH Na CH3O-Na+ CH3 CH3- O- CHCH3 + NaBr

CH3

b. C6H5OCH2CH3

OH O- Na+ O-CH2CH3
Na CH2CH3Br
+ NaBr

c. (CH3CH2CH2CH2)2O

CH3CH2CH=CH2
180 Co

CH3CH2CH2CH2OH

CH3CH2CH2CH2-O-CH2CH2CH2CH3
140 oC